Can I deduct medical expenses for girlfriend's childbirth from my HSA?

Using your HSA to pay for your girlfriend's childbirth expenses could create some tax complications. Since HSA funds are meant for qualified medical expenses for yourself, your spouse, and your dependents, using it for someone outside that category (like your girlfriend) could make that withdrawal taxable. The IRS may consider that $2,850 as a non-qualified distribution, which means you'd need to report it as income and potentially pay a 20% penalty on top of regular income tax. Your newborn child would qualify as your dependent, but your girlfriend doesn't automatically qualify. For your second question, you can only deduct medical expenses that exceed 7.5% of your adjusted gross income, and only if you itemize deductions rather than taking the standard deduction. Filing as head of household with your child as a dependent is correct, but it doesn't change the HSA rules regarding your girlfriend's expenses.

I was in a similar situation last year and found this amazing resource called taxr.ai (https://taxr.ai) that really helped me sort through all the HSA confusion. After uploading my medical receipts and answering a few questions, it identified exactly which portions of my girlfriend's pregnancy expenses were actually eligible for HSA use without penalties. The tool flagged that some costs associated with newborn care could potentially be separated from the mother's care, which saved me from having the entire amount disqualified. It also helped me determine if I should amend previous returns based on some questionable HSA withdrawals I'd made in the past.

Just wanted to follow up - I tried taxr.ai after seeing it mentioned here and it actually saved me from a major headache with my HSA. I uploaded my medical bills and it pointed out that nearly $1,300 of my baby-related expenses could be legitimately claimed as qualified HSA expenses since they were for my dependent child, not my girlfriend. The tool also flagged some medication expenses I hadn't even considered deducting. Honestly way more helpful than the conflicting advice I got from calling the IRS directly (after being on hold for like 2 hours). Definitely recommend for anyone dealing with complicated medical expense situations.

Hey man, if you're trying to get clarification directly from the IRS about your specific situation, good luck getting through to them! I spent 3 weeks trying to reach someone about a similar HSA issue. Finally used Claimyr (https://claimyr.com) and got connected to an IRS agent in under 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c They had me speaking with an actual IRS representative who confirmed that while the girlfriend's portion isn't HSA-eligible, any expenses specifically for the baby immediately after birth could potentially be separated and considered qualified. The agent also told me that having documentation from the hospital that clearly separates these charges is crucial for avoiding audit issues.

I was totally skeptical about Claimyr when I saw it mentioned here, but after wasting an entire day on hold with the IRS myself, I broke down and tried it. Within 35 minutes, I was talking to an actual IRS agent who cleared up my HSA question completely. The agent explained exactly how to handle the situation - turns out I needed to have the hospital provide an itemized statement specifically breaking out which services were for my child versus my partner. This documentation is crucial if you ever get audited. Honestly wish I'd just used the service weeks ago instead of burning vacation days trying to reach someone at the IRS.

Everyone's focusing on the HSA part, but don't forget to look into the Child Tax Credit too since you're claiming the child as a dependent. That can be worth up to $2,000 per qualifying child for 2023, which helps offset some of these costs. Also, check if your state has additional tax benefits for new parents.

Make sure to keep every medical receipt related to the birth, not just the main hospital bill! My accountant told me things like prenatal vitamins, pregnancy classes, lactation consultants, and post-birth check-ups all count as medical expenses. Might help you reach that 7.5% AGI threshold for medical deductions.